Installing Microsoft Windows onto DigitalOcean Droplet

You no longer need to open a ticket to request your Droplet to be booted into “Rescue Mode”, you may do it yourself via your DigitalOcean client area!

Installing Microsoft Windows Operating System to DigitalOcean’s Droplet is impossible using conventional methods due to the inability to mount an installation ISO and lack of a KVM providing a virtual keyboard (ie. Send Ctrl + Alt + Del, etc.).

We, the volunteers here at WhatUpTime, have built special templates allowing Windows to be installed via DigitalOcean’s Recovery ISO; their Recovery ISO is available with all of their droplets, however you need to request it to be mounted via support ticket.

The guide below will walk you through the entire process, from beginning to end. Once you have reached the end of the guide your server will be successfully running Microsoft Windows Operating System.

The Guide

Create Droplet – Once you have logged in, you will need to choose “Create Droplet”.

Choose an Image – Ubuntu 16 is recommended, however any Operating System may be chosen.

Choose a Size – The template will successfully install to all size Droplets, however depending on your workload you may need a larger size due to CPU & RAM needs.

Choose a Datacenter Region – You may choose any location you desire to have your Droplet located.

Choose a Hostname – Here you will choose the name for your Droplet.

Create – Once you have selected the operating system, size and location for your Droplet you will need to choose “Create” at the bottom of the page.

As you may have noticed there were additional options on the Droplet creation page, please ensure to do NOT choose “Backups” or “User Data” as they may interfere with the installation of Microsoft Windows and cause the installation to fail.

You can certainly enable “IPv6” and “Private Networking”, both should work without issue once Microsoft Windows has been installed.

Recovery ISO & Support Ticket – Once your Droplet has been successfully created a support ticket will need to be created to request DigitialOcean’s Recovery ISO be mounted to your Droplet.

Locate Support Ticket Creation Page – Choose “Support” at the top of DigitalOcean’s control panel webpage.

Support Tickets – Once you are inside DigitalOcean’s “Support Center” you need to choose “Support Tickets” at the top right of the page.

Create Ticket – Depending on the age of your account you may need to choose “Create Ticket” (Blue Button) at the top right of the control panel web page.

Create New Support Ticket – Once you have arrived on the “New Support Ticket” page inside DigitialOcean’s control panel you will need to fill in the page similar to the following screenshot.

Submit Ticket – Once you have completed filling in the Support Ticket Request to be similar to the above screenshot you will need to choose “Submit Ticket” (Blue Button) at the bottom right of the page.

Depending on the time of day it may take several hours for DigitalOcean’s Support Team to respond to your Support Ticket.

Ticket Response – DigitalOcean’s Support Team will eventually respond to your ticket noting the Recovery ISO has been mounted to your Droplet.

Power Off & Power On Your Droplet – Once the recovery ISO has been mounted for you by DigitalOcean’s Support Team you will need to power your Droplet off and then power it back on all via their web control panel.

Choose “Switch Off”

Choose “Turn Off” – When you have chosen “Off / Switch Off” you will be presented with an warning message providing some good information. I would recommend reading the message thoroughly so you are well informed for the future.

When you have read the entire message continue by choosing “Turn Off”.

It will take a few moments for your Droplet to completely power off.

Choose “Switch On”

As with powering off, it will take a few moments for your Droplet to power on.

Accessing Your Droplet’s Console – DigitalOcean provides console access for all of their Droplets (It provides similar access to have a monitor, keyboard and mouse attached) which will be used to install Microsoft Windows onto your Droplet.

Opening the Console – Choose “Console” at the top, right side of DigitalOcean’s web control panel for your Droplet.

A New Browser Windows Opens – Once you have chosen “Console” as detailed above a new browser window will open presenting you with your Droplet’s console.

In the event your console windows doesn’t look nearly identical to the above you will want to respond to your Support Ticket requesting assistance from DigitalOcean’s Support Team in regards to booting your Droplet into the recovery ISO.

Access Interactive Shell – Your recovery environment now has network access allowing us to continue with the downloading and installation of Microsoft Windows to your Droplet.

Choose “6” on your keyboard to choose option #6 (“Interactive Shell [/bin/bash]”) and then choose “Enter” on your keyboard to run the command.

Installing Microsoft Windows – To begin the Windows installation you will need to input the following command into your Droplet’s console. Please ensure the command matches perfectly otherwise your installation will likely fail.

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2) The Recovery ISO provided by DO does have the option to install SSH Server. You can install the SSH Server, connect to your Droplet running the Recovery ISO via SSH and run the same commands (You can copy & paste).

Great write-up! I’m wondering if there is a way to move an existing installation (physical or virtual) onto the cloud? Would be great if I could move a couple of my servers and boot them up so they run as a droplet on DigitalOcean.

It would theoretically be possible, however it may take some trial and error to do it.

The primary things that come to mind..

1. Force install VirtIO drivers (Assuming this is for Windows)
2. Shrink the c:\ partition using Windows Disk Manager
3. Live boot to Linux ISO/rescue mode
4. Use DD to take a complete image of the disk
5. Once you have your image you can install it to DigitialOcean similar to the above

The biggest concern would be the fact your disk image may have issues due to it being a much larger physical disk when you are creating the image than you will have with your new Cloud Server/VPS.

Thanks for the reply. I think you might be right in your assessments regarding this matter. There has to be an easy way to do this? We should definitely team up here to find a solution. If you find this case interesting of course.

Yes & No, when you upgrade your Droplet you are given the option to increase your disk size or leave it as the current size. In order to downgrade in the future you will need to avoid upgrading the disk size and always keep it the same.

So if a user is running a $20 droplet and they want to upgrade to any higher tier droplet, while maintaining their working windows installation, they need to make sure to choose the “CPU and RAM only” option when upgrading.

Thanks for answering all these questions and for providing such an awesome workaround.

I did hit 1 snag. Not your fault, but worth mentioning: You cannot snapshot the droplet and restore it later. Will not work. Talked to support and they said restoring a snapshot does linux-y things and if it cant do it, it will fail. So you must make these boxes one at a time and involve support for recovery iso.

The download links for the templates have recently changed, however the mirrors are still very much online.

In order to obtain the new download links you will need to submit a donation using the form just above the comment section here on this article. Once your donation has been received you will receive an activation link via email allowing you to access the remaining parts of the article and updated download links for each of the templates.

Hi,
I successfully completed Step #23 (my droplet can connect to the internet now in the console) but when I try using RDP, it just won’t log in. Is this how I am supposed to input my credentials?
Computer: [my droplet’s public IP]
User name: root
Password: [the password when I created my droplet]

The credentials you need to use when logging into Remote Desktop are outlined above; it will _not_ be the username & password received from DigitalOcean.

Above in the guide where you ascertained the link to download/install the template you will find the login credentials directly below in a yellow box; the credentials vary from one template to the next in some cases.

Just wanted to say that it all worked for me on Digital Ocean droplet. Thanks for setting up this excellent tutorial and Windows templates to use in the installation 🙂 Only issue I ran into was when I configured the IPv4 address manually. It still wasn’t working until I realized the IPv6 was enabled on the Windows template but not on the droplet. Once I turned off IPv6 in Windows, the network connected and I’m setting everything up right now… Thanks again…